inverse electron demand cycloadciition of isoquinolinium salts to dienophiles bearing chiral auxiliaries to produce homochiral tetralins are described. The optical purity of the product ranges from 5% to 95+% depending on the nature of the chiral auxiliary.
Cycloaddition of ethylene derivatives with isoquinolinium salts
✍ Scribed by C.K. Bradsher; F.H. Day
- Publisher
- Elsevier Science
- Year
- 1971
- Tongue
- French
- Weight
- 91 KB
- Volume
- 12
- Category
- Article
- ISSN
- 0040-4039
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📜 SIMILAR VOLUMES
Isoqulnolinium salts \*re known to undergo ring opening when strong electron withdrawing groups are directly bonded to the nitrogen atom. 3a-d We now wish to report a new and unusual ring opening of alkyl isoquinolinlum salts. Treatment of such salts with sodium
1n 1935 Krohnke' reported that benzaldehyde condensed with Z-benzylisoquinolinium bromide (1, R = CHzC9H5), in the presence of alkali, to yield, after acidification with HBr, an alcohol, formulated as (2). Since it is probable that the pseudobase (3, R = CB2CSH5) is formed from (1) and the alkali,
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